Personal experience with mental health (MH) challenges has been characterized as a concealable stigma. Identity management literature suggests actively concealing a stigma may negatively impact wellbeing. Reviews of workplace identity management literature have linked safety in revealing a stigma to individual performance, well-being, engagement and teamwork. However, no research to date has articulated the factors that make sharing MH challenges possible. This study employed a comparative case study design to explore the sharing of MH challenges in two Australian MH services. We conducted qualitative analyses of interviews with staff in direct service delivery and supervisory roles, to determine factors supporting safety to share. Workplace factors supporting safety to share MH challenges included: planned and unplanned “check-ins;” mutual sharing and support from colleagues and supervisors; opportunities for individual and team reflection; responses to and management of personal leave and requests for accommodation; and messaging and action from senior organizational leaders supporting the value of workforce diversity. Research involving staff with experience of MH challenges provides valuable insights into how we can better support MH staff across the workforce.